For around $180, I’ve seen worse. Will it crease? Obviously. But it’s a durable shoe. I’ve had pairs last for "years" with casual wear. It’s an investment in your wardrobe, not just a fleeting trend. Alright, so I just got my hands on this pair of Air Jordan 1 High 'Chicago' — and wow, the box feels classic. First look? The silhouette is just ... perfect. That red, white, and black combo is iconic for a reason. At around $180 USD, you're paying for the legacy. The leather feels decent — not super premium, but it's got that nice, stiff structure that defines the "Air Jordan 1 High". I'm excited to see these on feet. Who should buy this ‘Air Jordan 1 High’? Anyone building a foundational sneaker rotation. It’s essential. It works for almost any casual outfit. Who should "skip" it? If you’re new to sneakers and on a tight budget, maybe start with something more comfortable. Also, if you hate breaking shoes in – the stiff start might frustrate you. Pulling these Air Jordan 1 Highs out, the color is even richer in natural light. On-foot, they make you stand taller, literally. The build quality is dependable for the price point in the Jordan line. A real pro is the sheer number of outfits they complement. A con? The lack of modern cushioning is noticeable if you're used to newer tech. I'd say these are essential for any Jordan collector's foundation. For a pure performance or comfort seeker, maybe pass and grab something else.